‘Simon says,’ or rather, creates: Cindy Simon spreads joy through art

Quinn Casey

Cindy Simon installs her latest public artwork on Spring Street. (Photo courtesy of Cindy Simon.)

Around the corner of the Carol Girard and Cynthia Stewart Simon Squash Center stands a rather unsightly fence to protect passersby from icicles falling off the building’s roof. Cindy Simon, the eponym of the Squash Center, spent her annual visit to Williamstown decorating the fence with handmade, colorful yarn creations. As a self-described “found objects creative,” Simon has shared her public art installations with the community for years, but her fondness for making people smile through art has extended far beyond the Purple Valley. 

Cindy Simon had not heard of the College before meeting her husband, William Simon Jr. ’73, a former captain of the squash team who teaches a Winter Study course every year. She grew up in Oak Park, Ill., a suburb of Chicago, and followed generations of her family when she attended Indiana University Bloomington. “[My family] had never heard of Williams, and, honestly, I hadn’t either,” she said. 

While the College was not a part of her early life, her paternal grandmother bestowed upon her the gift of artistic creation at a young age. “She taught me how to sew on a sewing machine, how to crochet, how to needlepoint… She did a lot of homespun work,” Simon said. Simon, however, did not have much time to develop her creative skills further, as she completed her undergraduate education and began a career in investment banking. 

The investment banking world was a male-dominated arena in the 1970s, and Simon had to advocate for herself to break through. When she applied to work at Kidder Peabody, which was a securities firm, the man conducting her interview suggested that she start as a secretary. “I said, ‘Oh, no, no, no, no. I want to be a trader on the trading desk,’” she said. “I worked at Kidder Peabody as a convertible bond trader for 10 years.” 

Simon was introduced to her husband — and subsequently the College — while on the trading floor. “I sat across the trading desk from Bill’s brother, Peter, and he eventually introduced me to Bill,” she said. While the pair had never met in-person, they were familiar with each other’s voices because the members on the trading desk shared a phone line. “I talked to Bill on the phone a lot when he would call to speak with Peter,” she said. “I knew what he sounded like, but had not seen him.” 

The couple married in 1987, and Simon saw the College for the first time shortly after. “The first time I saw Williams, [my husband] was all proud of it because Williams had just installed a brand new basketball court that year — [Chandler] Gymnasium,” she recalled. “I said, ‘Oh, well, my high school stadium is bigger than this.’” 

While the Chandler court did not compare to Indiana’s Big Ten stadium, Simon grew to appreciate the College as she visited her son, Griffith Simon ’15, and spent time on campus while her husband taught his Winter Study course. “You would think January wouldn’t be the time you come around to appreciate Williams,” Simon laughed. “I really fell in love with the quietness and the solitude.” 

Over the next ten years, Simon rediscovered her artistic side, beginning to create art using found objects and various materials. “Things that you may consider garbage, I find inspirational,” she said. The hobby came in handy when she found herself with an abundance of free time during Winter Study. “It gives me something to do that’s productive while I’m there for the month,” she said.

Simon installed the first public art installation on campus in 2018. Since then, she has decorated the trees outside Lasell Gymnasium with purple and yellow trinkets, yarn, bells, crocheted blankets, and more. The current installation was not planned, but rather a response to the mundane aesthetics of the fence. “I wanted to try something different, and when I saw the fence, I thought, ‘That’s an area that could use some beautification,’” she said. 

Her work has been warmly received and remembered by students. This January, one student saw Simon decorating the fence and told her that a previous year’s art installation encouraged them to attend the College. “They said, ‘When I came across your installation, it was so friendly, fun, and fanciful. It just left me with a really good impression of my experience at Williams,’” Simon recalled. “That really meant a lot to me.” 

Outside of the College, Simon uses her talents to build community and make a difference in people’s lives. With her friend Dorothy Miyake, she co-founded a nonprofit called Dollies Making A Difference after an earthquake devastated Haiti in 2010. Following the motto “to give is to receive,” thirty to forty women met weekly in Simon’s dining room to sew dolls and teddy bears that they donated to children all over the world. “It wasn’t just about sewing dollies or thinking of the kids,” Simon said. “It was [also] about having a community of women to sit, to share, and to talk with.” 

After ten years and over 17,000 dollies and teddy bears made, Simon discontinued the organization in 2020. “For us, making the dollies was as important as giving the dollies away,” Simon said. “It was about the feeling you get when you extend something handmade to someone else.” 

Simon reflected on her fondness for creating and sharing her art with others. “I think you end up doing your best work when you enjoy doing it,” she said. “If you can find something that makes you want to get up in the morning — even if it’s stringing together plastic bottle caps like I do — nurture that.” 

Simon hopes her handmade art spurs joy in those who come across it. “If you walk by and see my art and it puts a smile on your face, then my job is done.”